Moving towards clinical translation of bioorthogonal chemistry: preparation and testing of a 99mTc instant kit for imaging and treating bone injury using inverse-electron demand Diels-Alder (IEDDA) chemistry

2019 ◽  
Vol 72-73 ◽  
pp. S30
Author(s):  
N. Mercanti ◽  
H. Bilton ◽  
N. Janzen ◽  
J. Valliant
Keyword(s):  
Diels Alder ◽  
Clinical Translation ◽  
Bioorthogonal Chemistry ◽  
Inverse Electron Demand ◽  
Bone Injury ◽  
Electron Demand

Preparation of tetrazine-containing [2 + 1] complexes of 99mTc and in vivo targeting using bioorthogonal inverse electron demand Diels–Alder chemistry

2017 ◽  
Vol 46 (42) ◽  
pp. 14691-14699 ◽  
Author(s):  
Abdolreza Yazdani ◽  
Nancy Janzen ◽  
Shannon Czorny ◽  
Robert G. Ungard ◽  
Tanya Miladinovic ◽  
...  
Keyword(s):  
Bone Turnover ◽  
Diels Alder ◽  
Bone Lesions ◽  
Targeted Imaging ◽  
Bioorthogonal Chemistry ◽  
High Bone Turnover ◽  
Inverse Electron Demand ◽  
High Bone ◽  
Electron Demand

A new 99mTc-labelled tetrazine for targeted imaging using bioorthogonal chemistry was developed and evaluated in vivo using a trans-cyclooctene derived bisphosphonate targeting regions of high bone turnover and bone lesions.

Potassium Arylethynyltrifluoroborate as an Unstrained Dienophile for Ultrafast and On Demand Activation of Bioorthogonal IEDDA Reactions

2019 ◽  
Author(s):  
Zijian Guo ◽  
Bruno Oliveira ◽  
Claudio D. Navo ◽  
Pedro M. S. D. Cal ◽  
Francisco Corzana ◽  
...  
Keyword(s):  
Protein Modification ◽  
Cross Reactivity ◽  
Diels Alder ◽  
Inverse Electron Demand ◽  
On Demand ◽  
Strained Alkenes ◽  
Electron Demand

<p>Strained alkenes and alkynes are the predominant dienophiles used in inverse electron-demand Diels-Alder (IEDDA) reactions, however, their instability, cross-reactivity and accessibility are problematic. Unstrained dienophiles, although physiologically stable and synthetically accessible, react with tetrazines significantly slower relative to strained variants. Here we report the development of potassium arylethynyltrifluoroborates as unstrained dienophiles for ultrafast, chemically triggered IEDDA reactions. By varying the substituents on the tetrazine (e.g. pyridyl- to benzyl-substituents), cycloaddition rates can vary from nearly spontaneous (<i>t</i><sub>1/2</sub>≈ 9 s) to no reaction with the unstrained alkyne-BF3 dienophile. The reported system was applied to protein modification and enabled mutually orthogonal labelling of two distinct proteins.</p>

Potassium Arylethynyltrifluoroborate as an Unstrained Dienophile for Ultrafast and On Demand Activation of Bioorthogonal IEDDA Reactions

2019 ◽  
Author(s):  
Zijian Guo ◽  
Bruno Oliveira ◽  
Claudio D. Navo ◽  
Pedro M. S. D. Cal ◽  
Francisco Corzana ◽  
...  
Keyword(s):  
Protein Modification ◽  
Cross Reactivity ◽  
Diels Alder ◽  
Inverse Electron Demand ◽  
On Demand ◽  
Strained Alkenes ◽  
Electron Demand

<p>Strained alkenes and alkynes are the predominant dienophiles used in inverse electron-demand Diels-Alder (IEDDA) reactions, however, their instability, cross-reactivity and accessibility are problematic. Unstrained dienophiles, although physiologically stable and synthetically accessible, react with tetrazines significantly slower relative to strained variants. Here we report the development of potassium arylethynyltrifluoroborates as unstrained dienophiles for ultrafast, chemically triggered IEDDA reactions. By varying the substituents on the tetrazine (e.g. pyridyl- to benzyl-substituents), cycloaddition rates can vary from nearly spontaneous (<i>t</i><sub>1/2</sub>≈ 9 s) to no reaction with the unstrained alkyne-BF3 dienophile. The reported system was applied to protein modification and enabled mutually orthogonal labelling of two distinct proteins.</p>

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